DND in Dragon Prince

Reborn in the world of the Dragon prince with a dnd character sheet of every class Jack is going to grind his way to level 20 in every class and make sure he survives (i have not read the books nor plan to so this is entirely based of the show and the wiki page(Also instead of xp Jack is going to work in milestones, meaning each significant thing he does he gains a lvl(May change this depending on how slow it makes the story)))